Director, Customer Success Operations & Education

Redwood Software is the leading orchestration platform for the autonomous enterprise, driving business transformation at the lowest total cost of ownership. Redwood empowers organizations to intelligently automate and orchestrate mission-critical business and IT processes across complex ERP, hybrid cloud, data and emerging agentic AI systems. Through its SaaS-first automation fabric—with AI embedded across the automation lifecycle—Redwood accelerates the path to autonomous operations. Backed by 30 years of experience and trusted by more than 50% of the Fortune 50, Redwood helps organizations unlock human potential to focus on innovation, growth and what’s next.

One Team. One Redwood
Make Your Own Weather
Obsess over Customer Success
Work the Problem
Be Curious
Own the Outcome
Respect Each Other

As a Director, Customer Success Operations & Education you will be responsible for leading the operating strategy, infrastructure, and customer learning ecosystem supporting Redwood’s global Customer Success organization. You will define how Redwood scales consistent, data-driven customer experiences across the full customer lifecycle, while ensuring customers, partners, and internal teams have the knowledge and resources needed to maximize the value of Redwood’s software solutions.

• Define and lead the global Customer Success operations strategy, roadmap, and governance model in alignment with Redwood’s customer and business objectives.
• Design and continuously improve the customer lifecycle operating model across onboarding, adoption, value realization, risk management, customer feedback, renewals, and advocacy.
• Establish scalable processes, service standards, playbooks, and engagement models that create consistent customer experiences across products, segments, and regions.
• Partner with Customer Success leadership to improve capacity planning, resource allocation, account coverage, and organizational scalability.
• Identify operational risks, process gaps, and areas of friction, and lead cross-functional initiatives to address them.
• Establish governance mechanisms that drive accountability, consistency, and continuous improvement across the Customer Success organization.
• Establish the Customer Success measurement framework and executive reporting strategy, connecting operational activity to customer and business outcomes.
• Define and monitor KPIs across onboarding, time-to-value, product adoption, customer health, satisfaction, retention, education engagement, and operational efficiency.
• Translate customer and operational data into actionable insights, recommendations, and investment priorities for senior leadership.
• Partner with Finance, Sales Operations, and Customer Success leadership to strengthen forecasting, resource planning, and performance visibility.
• Improve the quality, accessibility, and governance of customer data across systems and teams.
• Own Redwood’s global customer education vision and multiyear strategy across products, customer segments, partners, and stages of the customer lifecycle.
• Ensure education programs support faster onboarding, increased product adoption, stronger customer proficiency, and long-term value realization.
• Oversee scalable learning experiences, including instructor-led training, digital learning, webinars, product documentation, video tutorials, learning paths, and certification programs.
• Develop a role- and competency-based learning framework supporting customers from new users through advanced technical practitioners.
• Evaluate opportunities to expand certification, partner enablement, and other scalable or revenue-generating education offerings.
• Champion modern learning approaches, including AI-assisted content development, personalization, self-service learning, and learning automation.
• Develop a structured Voice of the Customer program that captures, analyzes, and communicates customer insights across the organization.
• Represent customer needs and operational priorities in product planning, go-to-market initiatives, and executive decision-making.
• Partner with Product and Engineering to connect customer feedback, adoption data, and learning needs to product-roadmap decisions.
• Collaborate with Professional Services, Support, Marketing, and Sales to create a cohesive customer journey and eliminate gaps between functions.
• Build strong relationships with strategic customers and partners to understand evolving needs and validate program direction.
• Present strategies, performance insights, risks, and recommendations to executive stakeholders.
• Own the strategy, evaluation, implementation, adoption, and optimization of Customer Success and customer education technologies.
• Lead the effective use of customer success platforms, learning management systems, analytics solutions, feedback platforms, and content-development tools.
• Establish system governance, data standards, integrations, and workflows that improve team productivity and customer visibility.
• Evaluate emerging technologies, including AI-enabled platforms, that can improve customer engagement, predictive insights, learning effectiveness, and operational scale.
• Manage key technology vendors, contracts, budgets, and implementation partners.
• Lead, develop, and scale a multidisciplinary team that may include Customer Success operations professionals, instructional designers, trainers, learning-program managers, and content creators.
• Build an organizational structure and talent strategy that supports Redwood’s growth and evolving customer needs.
• Coach and develop managers and individual contributors while establishing clear expectations, career paths, and succession plans.
• Foster a culture of customer focus, accountability, innovation, collaboration, and continuous improvement.
• Develop annual operating plans, budgets, staffing models, and investment recommendations for Customer Success Operations and Education.
• Manage competing priorities across multiple strategic initiatives while maintaining strong execution and stakeholder alignment.
• Drive measurable improvements in Customer Success operating-model adoption, customer-health visibility, onboarding and time-to-value, product adoption, customer proficiency, education outcomes, operational efficiency, customer feedback integration, satisfaction, retention, and long-term customer value.

• Bachelor’s degree in Business, Education, Instructional Design, Operations, Technology, or a related field; master’s degree preferred.
• At least 10 years of progressive experience across Customer Success operations, customer education, enablement, training, instructional design, or related functions.
• Five or more years of leadership experience, including leading managers, multidisciplinary teams, or globally distributed functions.
• Demonstrated success defining and executing Customer Success operations or customer education strategies within a SaaS, enterprise software, or technology organization.
• Proven ability to build scalable operating models, processes, programs, and systems that improve customer and business outcomes.
• Experience partnering with executive leaders and influencing strategy across Customer Success, Product, Engineering, Sales, Marketing, Professional Services, Support, and Finance.
• Strong understanding of the enterprise customer lifecycle, including onboarding, adoption, value realization, risk management, retention, and advocacy.
• Experience establishing performance frameworks and using data to evaluate customer health, operational efficiency, learning effectiveness, and business impact.
• Strong knowledge of learning management systems and digital learning platforms; experience with Skilljar preferred.
• Experience selecting, implementing, or optimizing Customer Success platforms, customer-feedback systems, analytics tools, and content-authoring technologies.
• Demonstrated ability to manage organizational change, complex cross-functional programs, budgets, vendors, and competing priorities.
• Exceptional executive communication, stakeholder-management, and presentation skills.
• Strong business judgment with the ability to move effectively between long-term strategy and operational execution.
• Passion for simplifying complex technology and helping customers realize measurable value from enterprise software.
• Experience supporting global enterprise customers across multiple products, regions, or customer segments preferred.
• Background in automation, enterprise software, SaaS, ERP, or other technically complex product environments preferred.
• Experience building customer certification, partner education, or scaled digital-learning programs preferred.
• Familiarity with AI-enabled customer engagement, learning personalization, content development, or operational analytics preferred.
• Track record of connecting education and Customer Success initiatives to improved adoption, time-to-value, retention, expansion, or customer satisfaction preferred.

Pay Transparency: The typical base salary range for this position is CAD $150,000 - $170,000 annually. The range represents base salary only, and does not include company bonus, incentive for sales roles, equity or benefits, as applicable. Final compensation will be determined based on the candidate's skills, experience, and relevant qualifications.

Vacancy Status: Existing vacancy

AI Transparency Disclosure: As part of our commitment to hiring transparency and in compliance with Ontario law, please be advised that we utilize artificial intelligence (AI) tools during our interview process. Specifically, we may use an AI-enabled notetaking assistant to help capture and summarize interview discussions. This tool is used solely to assist our hiring team in summarizing candidate information; all final hiring and selection decisions are made exclusively by individuals on the hiring team.